McCaskey, son of current Bears principal owner Virginia Halas McCaskey, is the oldest grandchild of George Halas and became president of the Bears in 1983 after Halas' death. McCaskey held that post until 1999, when he succeeded his father Ed as Chairman of the Board until 2011. He is the brother of current Bears Chairman George McCaskey.
Mike McCaskey was never a fan of Mike Ditka but kept the volatile Ditka on as coach with an extension in 1984 and was rewarded with a Super Bowl trophy the following season. McCaskey clashed repeatedly with Ditka on a variety of issues and finally fired Ditka after a disastrous 5–11 season in 1992.
McCaskey's first coaching hire, Dave Wannstedt, was a sought-after candidate that McCaskey was able to sign but the Wannstedt tenure was a steady downward spiral after a 1994 playoff appearance. Wannstedt was fired after 1998 and after a botched hiring of Dave McGinnis as head coach, McCaskey was stripped of much of his operational responsibilities and limited to the position of chairman of the board.
McCaskey is an alumnus of the Weatherhead School of Management, at Case Western Reserve University. He served in the Peace Corps in Ethiopia and taught at the business schools at UCLA and Harvard University prior to becoming president of the Bears.
- Dan Pompei. "Michael McCaskey to retire as Bears chairman". Chicago Breaking Sports. April 21, 2010. Retrieved on August 5, 2010.
- Kelly, Michael. "Peace Corps Turning 40". Retrieved 2010-09-15.
- Steinbreder, John. "The Owners". Sports Illustrated. Retrieved 2010-09-15.